General, Organic, and Biological Chemistry - 4th edition
4th Edition
ISBN: 9781259883989
Author: by Janice Smith
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 14, Problem 59P
Interpretation Introduction
(a)
Interpretation:
The structure of products formed from dehydration of 3-hexanol needs to be determined.
Concept Introduction:
According to Zaitsev's rule, in elimination reaction the
Dehydration reaction is defined as removal of water molecule from a compound. An alcohol reacts with acid to from alkene as a dehydration product.
Interpretation Introduction
(b)
Interpretation:
The reason for the formation of both the products in same amount needs to be explained.
Concept Introduction:
According to Zaitsev's rule, in elimination reaction the alkene formed in major amount is the one which is formed due to the removal of hydrogen from the beta carbon atom with a smaller number of hydrogen atoms. Also, the alkene formed as major product is more substituted.
Dehydration reaction is defined as removal of water molecule from a compound. An alcohol reacts with acid to from alkene as a dehydration product.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
IV. Compounds A and B are isomers of the molecular formula C9H19Br. Both yield the
same alkene Cin an elimination reaction. Hydrogenation of C yields the product
2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?
2. Write the structure for the most oxidized organic product when each of the following is reacted with potassium dichro- mate. Write NR if no reaction occurs.(a) methanol (b) ethyl alcohol (c) 2,3,4-trimethyl-2-pentanol (d) 3-hexanol
3. Alcohols can be made by reacting alkyl halides with sodium hydroxide as follows: RX +. NaOH ROH + NaX
Give the names and formulas of the alcohols produced from the following alkyl bromides by this method:(a) 2-bromobutane(b) 2-bromo-3-ethylpentane (c) bromocyclopentane
1) The acid-catalyzed dehydration of 2-methyl-2-butanol yields two alkene products, what are the names of the two alkenes?
2) which of the two alkenes is the major product?
Chapter 14 Solutions
General, Organic, and Biological Chemistry - 4th edition
Ch. 14.1 - Prob. 14.1PCh. 14.2 - Prob. 14.1PPCh. 14.2 - Classify each hydroxyl group in sorbitol as 1°,...Ch. 14.2 - Prob. 14.3PCh. 14.2 - Prob. 14.4PCh. 14.3 - Prob. 14.2PPCh. 14.3 - Give the structure corresponding to each name a....Ch. 14.5 - Draw the products formed when each alcohol is...Ch. 14.5 - Prob. 14.6PCh. 14.5 - Prob. 14.7P
Ch. 14.5 - Prob. 14.4PPCh. 14.6 - Prob. 14.8PCh. 14.7 - Prob. 14.9PCh. 14.7 - Prob. 14.5PPCh. 14.7 - Prob. 14.10PCh. 14.7 - Name each ether. CH3OCH2CH2CH2CH3Ch. 14.7 - Prob. 14.11PCh. 14.8 - (a) Translate the hall and stick model of...Ch. 14.8 - Prob. 14.13PCh. 14.9 - Prob. 14.14PCh. 14.9 - Prob. 14.15PCh. 14.9 - Prob. 14.16PCh. 14.9 - Prob. 14.17PCh. 14.9 - Prob. 14.18PCh. 14.9 - Prob. 14.19PCh. 14.9 - Prob. 14.20PCh. 14.10 - Give the IUPAC name for each thiol.Ch. 14.10 - Prob. 14.21PCh. 14.10 - Prob. 14.22PCh. 14 - Classify each alcohol as 1°, 2°, or 3o a....Ch. 14 - Prob. 24PCh. 14 - Prob. 25PCh. 14 - Classify each halide hi A as 1°, 2°, or 3°. A is a...Ch. 14 - Prob. 27PCh. 14 - Draw the structure of a molecule that fits each...Ch. 14 - Draw the structure of the six constitutional...Ch. 14 - Draw the structure of the four constitutional...Ch. 14 - Draw the structure of l-propanethiol, a compound...Ch. 14 - Prob. 32PCh. 14 - Prob. 33PCh. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - Answer each question about alcohol B. Draw a...Ch. 14 - Prob. 37PCh. 14 - Give the IUAPC name for each alcohol.Ch. 14 - Prob. 39PCh. 14 - Prob. 40PCh. 14 - Prob. 41PCh. 14 - Prob. 42PCh. 14 - Draw the structures and give the IUPAC names for...Ch. 14 - Prob. 44PCh. 14 - Prob. 45PCh. 14 - Prob. 46PCh. 14 - Give the structure corresponding to each IUPAC...Ch. 14 - Give the structure corresponding to each IUPAC...Ch. 14 - Which compound in each pair has the higher boiling...Ch. 14 - Rank the compounds in order of increasing melting...Ch. 14 - Rank the following compounds in order of...Ch. 14 - Rank the following compounds in order of...Ch. 14 - Prob. 53PCh. 14 - Prob. 54PCh. 14 - Prob. 55PCh. 14 - Prob. 56PCh. 14 - Prob. 57PCh. 14 - Prob. 58PCh. 14 - Prob. 59PCh. 14 - Prob. 60PCh. 14 - Prob. 61PCh. 14 - Prob. 62PCh. 14 - Prob. 63PCh. 14 - Prob. 64PCh. 14 - Prob. 65PCh. 14 - Prob. 66PCh. 14 - Prob. 67PCh. 14 - Prob. 68PCh. 14 - Prob. 69PCh. 14 - Prob. 70PCh. 14 - Prob. 71PCh. 14 - Prob. 72PCh. 14 - Prob. 73PCh. 14 - Prob. 74PCh. 14 - Prob. 75PCh. 14 - Prob. 76PCh. 14 - Prob. 77PCh. 14 - Prob. 78PCh. 14 - Prob. 79PCh. 14 - Prob. 80PCh. 14 - With reference to the halogenated organic...Ch. 14 - Prob. 82PCh. 14 - Prob. 83PCh. 14 - Prob. 84PCh. 14 - Write out the chemical reaction that occurs when a...Ch. 14 - Prob. 86PCh. 14 - Prob. 87PCh. 14 - Lactic acid [CH3CH(OH)CO2H] gives sour milk its...Ch. 14 - Prob. 89PCh. 14 - Prob. 90PCh. 14 - Prob. 91PCh. 14 - Prob. 92PCh. 14 - Prob. 93PCh. 14 - Answer the following questions about alcohol B....Ch. 14 - Prob. 95CPCh. 14 - Dehydration of alcohol C forms two products of...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw the structures of (a) 6-methyl-3-heptanol and (b) trans-2-methylcyclohexanolarrow_forwardWrite the reagent or draw structures of the starting material or organic product(s) in the following reactions. If more than one product is formed, identify the major product where possible. (a) (b) HO OH OH H2SO4 ? Cl₂ ? FeCl3arrow_forwardWhich products are formed when hydrobromic acid is added to (a) trans-2-hexene, (b) 2-methyl- 2-pentene, and (c) 4-methylcyclohexene, and how many regioisomers can be formed in each case?arrow_forward
- Ethers (general formula R—O—R)have many important uses. Until recently,methyl tert-butyl ether (MTBE, right)was used as an octane booster and fueladditive for gasoline. It increases the oxy-gen content of the fuel, which reducesCO emissions. MTBE is synthesized bythe catalyzed reaction of 2-methylpropene with methanol.(a) Write a balanced equation for the synthesis of MTBE. (Hint:Alcohols add to alkenes similarly to the way water does.)(b) If the government required that auto fuel mixtures contain2.7% oxygen by mass to reduce CO emissions, how many gramsof MTBE would have to be added to each 100. g of gasoline?(c) How many liters of MTBE would be in each liter of fuel mix-ture? (The density of both gasoline and MTBE is 0.740 g/mL.)(d) How many liters of air (21% O₂ by volume) are needed at24C and 1.00 atm to fully combust 1.00 L of MTBE?arrow_forward4 But-2-enal, CH₂CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour. (a) But-2-enal exists as two stereoisomers. Draw skeletal formulae to show the structure of the two stereoisomers of but-2-enal. (b) (i) Describe a simple chemical test that would show that but-2-enal is an aldehyde. (ii) Explain why this test gives a different result with aldehydes than it does with keton (c) But-2-enal also reacts with sodium borohydride, NaBH4. (i) Identify the organic compound formed in this reaction. (ii) State the type of chemical reaction occurring. (d) Precautions must be taken to prevent but-2-enal catching fire. Construct a balanced equation for the complete combustion of but-2-enal, C₂HO.arrow_forwardDraw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product). (a) 3-Hexanol (b) 1-Methylcyclobutanol (c) 2-Methyl-2-butanol (d) 2-Propanolarrow_forward
- 5B In the following reactions, mixtures of alkenes and ethyl ethers are formed. Draw their structures. Explain which is or are likely to be the main product(s) in each reaction. In case of formation of two isomers of alkenes, explain which is formed in greater proportion CH3 CH3 H3C-C H -Br CH3 EtOHarrow_forwardThe addition reaction of an acid (HBr) to an alkene (CH3CH=CH2) follows Markovnikov's rule and involves: A) initial attack by Br– B) initial attack by Br• C) isomerization of CH3CH2CH2Br D) formation of a primary carbocation. E) formation of a secondary carbonation. (F) Formation of allyl carbocationarrow_forwardDraw all the alkyl halides with molecular formula C 5H 11Cl formed when pentane (CH 3CH 2CH 2CH 2CH 3) is heated with Cl 2.arrow_forward
- Draw the skeletal (bond-line) structures of all isomers of C4H8O (including configurational isomers) that contain an alkene and an ether. There should be 5 structures.arrow_forwardThe acid-catalyzed dehydration of 2,3-dimethyl-3-pentanol yields three alkene products. What are the names of the three alkenes? Which of the three alkenes is the major product?arrow_forward6) Complete the following reactions by giving the starting material, reagent or product. If there is no reaction, then write so. a) 2-bromobutane b) c) d) OH OH NaNH, ? Br NaOH HCI ? OCH 3arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY